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Personal Care Compositions with Silicones And

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Personal Care Compositions with Silicones And (19) & (11) EP 1 804 922 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61Q 19/00 (2006.01) A61Q 1/02 (2006.01) 13.02.2008 Bulletin 2008/07 A61Q 19/10 (2006.01) A61Q 5/02 (2006.01) A61Q 5/12 (2006.01) A61Q 15/00 (2006.01) (2006.01) (2006.01) (21) Application number: 05797352.1 A61Q 11/00 A61K 8/896 A61K 8/891 (2006.01) A61K 8/58 (2006.01) A61K 8/898 (2006.01) A61K 8/41 (2006.01) (22) Date of filing: 24.10.2005 (86) International application number: PCT/EP2005/011416 (87) International publication number: WO 2006/045583 (04.05.2006 Gazette 2006/18) (54) PERSONAL CARE COMPOSITIONS WITH SILICONES AND DIHYDROXYPROPYL TRIALKYL AMMONIUM SALTS KÖRPERPFLEGEZUSAMMENSETZUNGEN MIT SILIKONEN UND DIHYDROXYPROPYL- TRIALKYL-AMMONIUMSALZEN COMPOSITIONS DE SOINS PERSONNELS COMPRENANT DES COMPOSES SILICONES ET DES SELS DE DIHYDROXYPROPYL TRIALKYL AMMONIUM (84) Designated Contracting States: • MINER, Philip E. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Unilever Home&Personal Care USA HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI Trumbull, CT 06611 (US) SK TR • BARROW, Stephen Unilever Home&Personal Care USA (30) Priority: 25.10.2004 US 972483 Trumbull, CT 06611 (US) 08.09.2005 US 222189 • CHANDAR, Prem Unilever Home&Personal Care USA (43) Date of publication of application: Trumbull, CT 06611 (US) 11.07.2007 Bulletin 2007/28 • MCMANUS, Richard Unilever Home&Personal Care USA (73) Proprietors: Trumbull, CT 06611 (US) • UNILEVER PLC • HARICHIAN, Bijan London, Greater London EC4P 4BQ (GB) Unilever T. V. A. Company LLC Designated Contracting States: SantaBarbara, CA 93101 (US) CY GB IE • UNILEVER N.V. (74) Representative: Acham, Nicholas Clive 3013 AL Rotterdam (NL) Unilever Patent Group Designated Contracting States: Colworth House AT BE BG CH CZ DE DK EE ES FI FR GR HU IS IT Sharnbrook LI LT LU LV MC NL PL PT RO SE SI SK TR Bedford, MK44 1LQ (GB) (72) Inventors: (56) References cited: • HURLEY, Megan K. EP-A- 0 930 066 WO-A-90/03161 Unilever Home&Personal Care USA WO-A-96/35410 WO-A-97/07779 Trumbull, CT 06611 (US) US-B1- 6 869 977 Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 804 922 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 804 922 B1 Description Field of the Invention 5 [0001] The invention concerns personal care compositions formulated to impart moisturization and having excellent skinfeel properties. The Related Art 10 [0002] Dry skin is a problem in varying degree to most humans. This condition is particularly evident in winter. Personal care products such as skin creams/lotions, shampoos/ conditioners, toilet bars/shower gels and antiperspirants/deodor- ants are normally formulated with at least one material to address dry skin. Symptoms such as itching, flaking and a visually displeasing dermal appearance can all to some extent be modulated. [0003] There are three traditional classes of materials employed against the problem. Occlusives such as petrolatum 15 or silicone oils serve to inhibit loss of natural moisture. They form a barrier between the epidermis and the environment. Another approach is the use of keratolytic agents to enhance rate of dermal exfoliation. Alpha-hydroxy acids are the most common agents for achieving exfoliation. [0004] A third approach to dry skin is topical application of humectants. Hydroxylated monomeric and polymeric organic substances are generally used for this purpose. Glycerin known also as glycerol is one of the most effective humectants. 20 [0005] Quaternary ammonium compounds have recently been commercialized as moisturizers. One of these known under the trademark Honeyquat 50 with INCI name of Hydroxypropyltrimonium Honey has been reported to be a better humectant than glycerin at levels of 2%. See the Arch/Brooks brochure titled "Cosmetic Ingredients & Ideas®", Issue No. 2, August 2001. Honeyquat 50 is described as being derived from the reaction of pendent hydroxyl groups (on the disaccharide) of a "light" deodorized grade of honey with a chlorohydroxytrimethylammonium derivative. Another com- 25 mercial quaternary ammonium moisturizer is Cola™Moist 200 with INCl name of Hydroxypropyl Bis-Hydroxyethyldimo- nium Chloride. See the Colonial Chemical Inc. brochure titled "Cola™Moist 200", copyright 2004. U.S. Patent 6,869,977 B1 (O’Lenick, Jr. et al.) to Colonial Chemical Inc. discloses a related monocationic material described as a moisturizing agent. [0006] Many moisturizing actives impart to their formulas an aesthetically displeasing tack and/or sticky skinfeel. The 30 present invention sought to provide a silicone containing moisturizing personal care composition having consumer pleasing skinfeel properties. SUMMARY OF THE INVENTION 35 [0007] A personal care composition is provided which includes: (i) from 0.05% to 30% by weight of a dihydroxypropyl quaternary ammonium salt of structure AB, wherein A is a cationic charged component of the salt AB, 40 B is an anionic charged component of the salt AB, and A has a single quaternized nitrogen atom, at least two hydroxy groups and a molecular weight no higher than 250; (ii) from 0.05 to about 50% by weight of a silicone. 45 DETAILED DESCRIPTION OF THE INVENTION [0008] Now it has been found that the skinfeel properties of moisturizing silicone compositions can be improved through inclusion of dihydroxypropyl quaternary ammonium salts as detackifying agents. [0009] Thus, an important material of the present invention is dihydroxypropyl quaternary ammonium salts of structure 50 AB, wherein A is a cationic charged component of the salt AB, and B is an anionic charged component of the salt AB, A has one quaternized nitrogen atom, at least two hydroxyl groups and a molecular weight no higher than 50 but preferably no higher than 200, and optimally no higher than 170. [0010] Anionic charged component B may be organic or inorganic with proviso that the material is cosmetically ac- ceptable. Typical inorganic anions are halides, sulfates, phosphates, nitrates and borates. Most preferred are the halides, 55 especially chloride. Organic anionic counter ions include methosulfate, toluoyl sulfate, acetate, citrate, tartrate, lactate, gluconate, and benzenesulfonate. The number and charge of negatively charged component B will be sufficient to neutralize the positive charge of component A. [0011] A preferred embodiment of the quaternary ammonium salts is the dihydroxypropyl tri (C1-C3 alkyl or hydroxyalkyl) 2 EP 1 804 922 B1 ammonium salts. [0012] These salts may be obtained in a variety of synthetic procedures, most particularly by hydrolysis of chlorohy- droxyprppyltri(C1-C3 alkyl or hydroxyalkyl) ammonium salts. Ordinarily the C1-C3 alkyl or hydroxyalkyl constituent on the quaternized ammonium group will be methyl, ethyl, n-propyl, isopropyl, hydroxyethyl, hydroxymethyl and mixtures 5 thereof. Particularly preferred is a trimethyl ammonium group known through INCl nomenclature as a "trimonium" group. A most preferred species is 1,2-dihydroxypropyltrimonium chloride, wherein the C1-C3 alkyl is a methyl group. [0013] Another useful species of the quaternary ammonium salts is the material of structure (I). 10 15 20 [0014] Amounts of the quaternary ammonium salts may range from 0.05 to 30%, preferably from 0.1 to 25%, more preferably from 5 to 20%, optimally from 10 to 15% by weight of the composition. [0015] The moisturizing compositions of this invention will include a silicone. A wide variety of silicones including materials of liquid, solid or semi-solid consistency at room temperature can be useful for this invention. Liquid silicones 25 include silicone oils which may be divided into the volatile and nonvolatile variety. The term "volatile" as used herein refers to those materials which have a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably chosen from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms. Commercially available volatile silicone oils include DC 200, DC 244, DC 245, DC 344 and DC 345, all supplied by the Dow Corning Corporation; SF-1204, SF-1202 Silicone Fluids, GE 7207 and GE 7158 sourced 30 from GE Silicones; and SWS-03314 sourced from SWS Silicones Corporation. [0016] Useful nonvolatile silicone oils include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane co- polymers. The essentially nonvolatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from 5 x 10-16 to 0.1 m2/s at 25°C. Among the preferred nonvolatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from 1 x 10-5 to 4 x 10-4 m2/s at 25°C. Representative 35 commercial materials include polyalkyl siloxanes sold under the Viscasil Series from G.E. Silicones, and the DC 200 series sold by the Dow Corning Corporation. Polyalkylaryl siloxanes including polymethylphenyl siloxanes such as SF 1075 methyl-phenyl fluid and 556 Cosmetic Grade Fluid (sold by Dow Corning Corporation) may also be useful. Illustrative polyoxyalkylene ether copolymers are commercially available as SF 1066 from G.E. Silicones, and PEG-10 Dimethicone available from Shin-Etsu. 40 [0017] Another class of nonvolatile silicones are emulsifying and non- emulsifying silicone elastomers. Representative of this category is Dimethicone/Vinyl Dimethicone Crosspolymer available as Dow Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18. Silicone waxes such as Silwax WS-L (Dimethicone Copolyol Laurate) may also be useful. [0018] Amounts of the silicone may range from 0.05 to 50%, preferably from 0.5 to 40%, more preferably from 2 to 20%, optimally from 5 to 12% by weight of the composition.
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